38 Old Turnpike Road
Litchfield, Connecticut 06750
Reduced from $1,495,000
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,377
- Acres
- 4.53
- Year Built
- 1777
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
An exceptional property with a rare convergence of historic provenance and modern excellence. This magical setting comprises a c.1777 home (once a Tollhouse), that blends 18th c. character, masterfully rebuilt in 2023. Step inside to a main floor that includes, a Kitchen, Dining Room, Parlor, Living Room & Primary BR suite including 3 FP's and a 3-season Solarium/Mudroom, Laundry room (ne' Buttery) and 1/2 BA. The Upper level has 2BR's and full bath. There are warm pine wood floors throughout. The enchanting park like setting includes, 3 parcels= 4.5ac.+-, with a pond, babbling stream, a 2-car barn-style garage with a ~400sf upper level studio incl. a sitting and sleeping area, a heated in-ground pool, well-established perennial gardens and pathways, stone walls and a gently rolling hill that borders the Land Trust. It is Connecticut pastoral perfection at its finest. WAIT!!! There's more...An opportunity to start a new, on-site business, currently, a 400 sf Antique Shop. For the collector, artisan or entrepreneur, seeking a life-work retreat or just pure tranquility. This is a one-of-a-kind property with incredible flexibility, delivering, history, beauty & endless possibilities, it is an extremely RARE opportunity. Are you ready to live your next chapter! Set between the storied villages of Litchfield, Bantam, New Preston & Washington for shopping, dining, hiking, skiing, boating or just relaxing. Conveniently located near top-tier area independent schools
Key Facts
- City/Town
- Litchfield
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1777
- Days on Market
- 265 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 2,377 sq ft
- Lot Size
- 4.53 acres
- Garage / Parking
- 2 garage · 5 total
- Property Taxes
- $8,211 / Annually
Market Snapshot
The Litchfield Market
Single Family · trailing 12 months
Active Listings
19
7 under contract
Median List Price
$895,000
19 active listings
Median Closed Price
$522,000
74 sales
Median Days on Market
83
19 active listings
Median $ / Sq Ft
$376
19 active listings
Sale-to-List Ratio
100.0%
74 sales
How this home compares
List Price
$1.10M
vs $895,000 median
22.9% above median
Price / Sq Ft
$463
vs $376 median
23.1% above median
Days on Market
265 days
vs 83 days median
182 days longer than median
Based on 19 active and 74 closed sales (trailing 12 mo) of single family in Litchfield. Source: SmartMLS · As of July 28, 2026.
Location
38 Old Turnpike Road, Litchfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,609
- Property Taxes$684
- Insurance$367
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Litchfield
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1777
- New Construction
- No/Resale
- Living Area
- 2,377 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- BaseboardRadiator
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 3
- Laundry
- Main Level
- Laundry Location
- Formally the old Buttery
- Appliances
- Gas CooktopOven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- Crawl SpaceFull
- In-Law Apartment
- PossibleOver Garage
- Additional Rooms
- Sitting RoomSolarium
Exterior & Lot
- Lot Size
- 4.53 acres
- Zoning
- RR
- Garage / Parking
- 2 garage spaces5 total parking spacesBarnDetached GarageOff Street Parking
- Waterfront
- Direct waterfront
- Waterfront Details
- PondBrook
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- Yes
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- TerraceFruit TreesBarnGuttersGarden AreaStone WallPatio
- Lot Description
- TreedProfessionally LandscapedRolling
Listing & Financials
- Property Taxes
- $8,211 / Annually
- Days on Market
- 265
- MLS #
- 24136619
- MLS Status
- Active
Similar Properties
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Co-Listed By
Phil Fox
William Pitt Sotheby's Int'l
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 6:01 AM UTC.